Asymmetric allylboration and ring closing alkene metathesis: a novel strategy for the synthesis of glycosphingolipids.

Abstract

A novel strategy for the synthesis of D,L-glucosylceramide 1, a member of the glycosphingolipid class of natural products is described. Reagent-controlled asymmetric Brown allylboration gave excellent stereochemical control in the construction of adjacent stereocenters in the sphingoid base portion of the molecule. The trans-configured double bond was obtained as a single geometrical isomer by use of silicon-tethered olefin metathesis employing the Schrock carbene [(CF3)2MeCO]2Mo(=CHCMe2Ph)(=NC6H3-2,6-i-Pr2++ +) and in situ PhLi-induced ring-opening of the intermediate 5,6-dihydro-2H-1,2-oxasiline followed by protodesilylation with TBAF in DMSO. The synthesis was completed by long chain amide formation and global deprotection.

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@article{Barrett2000AsymmetricAA, title={Asymmetric allylboration and ring closing alkene metathesis: a novel strategy for the synthesis of glycosphingolipids.}, author={Anthony G. M. Barrett and J. C. Beall and D. Christopher Braddock and Karen A. Flack and Vernon C. Gibson and Matthew M Salter}, journal={The Journal of organic chemistry}, year={2000}, volume={65 20}, pages={6508-14} }